L-Lysine → 5-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoin

HRID 1287290

反応式

HRID 1287290 の反応式
CO[C:3](=[O:21])[C@H:4]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[NH2:5].N[C@H](C(O)=O)CCCCN.[CH3:32][N:33]=[C:34]=[S:35]>C(#N)C>[CH2:14]([O:13][C:11]([NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:4]1[NH:5][C:34](=[S:35])[N:33]([CH3:32])[C:3]1=[O:21])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 5962L-LysineHCID 11167Methyl isothiocyanateHCID 6994982methyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate

生成物 1

HCID 215076825-(4-Benzyloxycarbonylaminobutyl)-3-methyl-2-thiohydantoin収率 22.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of Nε-benzyloxycarbonyl-L-lysine methyl ester (4.66 g., 0.016 mol.) (prepared from L-lysine according to the method of Bergmann et al., J. Biol. Chem. 1935, 111, 245) in acetonitrile (20 ml.) was treated with methyl isothiocyanate (1.16 g., 0.016 mol.) and the mixture heated at reflux for 3 hours. The solvent was removed in vacuo and the residual oil triturated with ethanol to give a white solid which recrystallised from ethanol to give the title compound as colourless needles (1.2 g.) m.p. 135°C. (Found: C, 57.3; H, 6.4; N, 12.2; C16H21N3O3S requires: C, 57.3; H, 6.3; N, 12.5%).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. customthe residual oil triturated with ethanol
  5. customto give a white solid which
  6. customrecrystallised from ethanol

出典と根拠

ORDレコード
ord-ac5d9645333b464685fd8da40dd721f4
出典データセット
uspto-grants-1976_10
特許番号
US03984430

関連ノート

読み込み中…